As to how to decide month-to-month, just listen to the news, check the stock prices and yields, and see which looks like the best value at the time. No magic formula. You want to think about how fast your money can compound (is it a dividend grower?) and whether that industry is growing right now, etc.

What do I need to track for my 7 DRIP accounts? Can you direct me to a spreadsheet or document that could help me track my DRIPs for tax purpose?

No problem, thought you should know as a big DRIP fan yourself! I started my Sun Life DRIP a little over 3 months ago. My initial investment was a few thousand in Dec. 2009 after the sale of our condo; wanted to diversify from as you say, “the usual financials”. I also considered Sun Life better than MFC; although it “moves with this stock”; because of great market capitalization; long-term growth potential (with an again population) and of course, history of dividends. They have strong marketing campaigns coupled with a strong brand. I recall my purchase was below $29/share. One of my very first posts on my blog was about SLF and other stocks I took the DRIP plunge into. Anyhow, now trading about $32 :) I should get my first dividend statement after the payment date (March 31, 2010). That should include the details of DRIP transactions and any fees (although I hope, none, based what’s on the Sun Life website). Dividend will be $0.36; representing about 4.5% yield. Here is the detailed DRIP information:

http://www.cibcmellon.com/Contents/en_CA/English/InvestorCentre/Information/IssuerDetails/Sun_Life_Financial_Inc.html

Dividend reinvestment plan features:

Optional cash payment (OCP) Yes
Discounts on dividends reinvested Yes
Discount on OCP No
Automatic investment service
(pre-authorized chequing) No
Partial dividend reinvestment option No
Minimum for OCP Yes, $100 / contribution
Maximum for OCP Yes, $50,000 / annum
Sale of partial portfolio Yes
Single purpose RRSP No
Open to persons outside Canada No
Dividend payment schedule Quarterly
OCP schedule Quarterly
Certificates upon request Yes

Let me know if you want to know more about SLF. All the best ME. Stay in touch.

http://www.sunlife.com/global/v/index.jsp?vgnextoid=fd7e738556503210VgnVCM100000abd2d09fRCRD&vgnLocale=en_CA

From the Sun Life page above:
“Is there a cost to participate in the plan?
All fees, expenses and brokerage commissions payable in connection with the Plan will be borne by the Corporation other than brokerage commissions, plus any applicable taxes, payable on the sale of common shares held through the Plan.”

This was the main reason I decided to jump-in on SLF last year, not MFC that I was considering (also, not the latter because MFC cut their dividend last year! Ouch!). Cheers!